تفاعل #748258

معادلة التفاعل

sodium trimethylsilanolate

4-bromo-2,5-difluoronitrobenzene

→

5-bromo-4-fluoro-2-nitrophenol

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىA bright red suspension was formed
2. 2
   درجة الحرارةthe mixture was refluxed for 27 hours
3. 3
   تركيزconcentrated
4. 4
   workup.ADDITIONWater (6 mL) was added
5. 5
   استخلاصextracted with DCM (70 mL×2)
6. 6
   تركيزconcentrated

الإجراء التجريبي

A solution of 2 M sodium trimethylsilanolate (15.6, 31.1 mmol) in THF was added dropwise to 4-bromo-2,5-difluoronitrobenzene (2.47 g, 10.4 mmol) under a nitrogen atmosphere. A bright red suspension was formed, and the mixture was refluxed for 27 hours. The mixture was cooled to room temperature and concentrated. Water (6 mL) was added, and the solution was acidified with a 10% HCl solution, extracted with DCM (70 mL×2). The organic layers were combined and concentrated to give 5-bromo-4-fluoro-2-nitrophenol (5.05 g, 2.06%). MS m/z: 236 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 7.48 (d, J=5.87 Hz, 1H), 7.95 (d, J=8.41 Hz, 1H).

المصدر